Water → HCID 4407465, compound

HRID 1282151Notes

Reaction equation

HRID 1282151 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[C:14]1[S:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][N:18]=1.O>C(#N)C>[N+:19]([C:16]1[S:15][C:14]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[N:18][CH:17]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 182112-Bromo-5-nitrothiazole

Product 1

HCID 4407465HCID 4407465, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of piperazine (18.2 g) and potassium carbonate (12.6 g) in acetonitrile (150 ml) was added 2-bromo-5-nitrothiazole (14.7 g) at 40° C. and the mixture was stirred at 60° C. for 40 min. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a brown solid (11.2 g). The obtained brown solid was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1) to give the title compound (4.8 g) as yellow crystals.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1f034ad5380a42139e81ea159dd686c0
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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